Ever Dreamed of Running Your Business From the Road? Here's How I Do It ...




by Jess Ekstrom

CEO and Founder of HeadbandsOfHope.com, Speaker and Author.

Five years ago, my parents sold their business, their house and everything they owned and bought an RV. To date, they’re still traveling around (and they’ve become park rangers)! I'm in awe of their lifestyle, in terms of how they can just pack up and go wherever they want while still retaining the comfort and familiarity of their “home” inside their RV. So, my husband and I decided that when we retired, that’s what we’d do, too.


Only, a small problem: Being 28 years old, we’re not even close to retirement.


In fact, I'm doing my career full-tme, having run my business, Headbands of Hope for seven years now. When I started traveling a lot for speaking engagements, I built out a strong team and started delegating tasks so I could do more of the creative work I love while also being able to travel for gigs. Little did I know, I was slowly preparing myself and my team for my constant travel on the road.


One March morning last year, my husband and I decided that “one day” didn't exist so we started planning how we were going to live in an Airstream full-time. After 10 months of planning, we leased out our place and put our stuff in storage and hit the open road.


Being mobile has not only been great for my speaking engagements and Headbands of Hope donations at children’s hospitals, it has been surprisingly easy to run my company from the road. If anything, I believe I’ve become a better leader by instilling responsibility in my team and creativity, because of my need to go into airplane mode more often.


Here are some steps I've taken to help me run my business from the road:


1. Stay connected.

One of the first purchases we made was an installation of Airstream Connected. This service basically turns your Airstream into a wifi hotspot. As a result, I’ve been able to look outside my window at the Rocky Mountains while also sending emails. This wifi hotspot has also allowed us to use our Apple TV when we need a break from the wilderness scenery.


I’d also suggest getting a cellular plan with unlimited data so you can use your phone as a hotspot when you need it. I use the app Sensorly to test and see if we’ll have service where we’re heading so I can alert my team if I'll be unreachable.


2. Hire a virtual assistant.

Before I left, I started working with a virtual assistant to manage my inbox and calendar. I can’t tell you what a game-changer it is to have someone in your inbox responding to things she can, forwarding the things she can't do to the appropriate people and starring anything she needs help with. One of my biggest issues is being addicted to email, so hiring a VA really helped me step away from it because I know if there’s something urgent, she’ll tell me.


3. Drop into coworking spaces.

As I’m sure you’ve seen, WeWork is popping up everywhere. With a global pass, you can pop into any WeWork location to attend to urgent tasks. This has been great when I’m near a major city and need a full day of strong wifi (and strong coffee). If you don’t want to commit to a global pass yourself, you can always buy day passes at various coworking spaces across the country.


4. Be “stingy” with your time.

Before I moved into the Airstream, I would say yes to anyone who wanted to “pick my brain” for 15 to 30 minutes. But when you’re on the road, scheduling meetings can be challenging because you want to make sure you’re within cell service and have wifi, not to mention the fact that you might want to go on a hike when important calls are coming in during the day.


I didn’t realize how much those meetings were time-robbers for me. Now, I can get into “work mode” and have a few hours of uninterrupted work, then go exploring. When I was at home, it used to take me an entire day to do the same amount of work because I was always stepping away for a call or a meeting.


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